4-Benzylpiperidine → 1-Benzyl-3-(SR)-(4-benzylpiperidin-1-ylmethyl)-4-(SR)-phenyl-pyrrolidine
Reaction equation
[CH2:1]([N:8]1[CH2:12][CH:11]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:10]([CH:19]=O)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:21]([CH:28]1[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]1)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>>[CH2:1]([N:8]1[CH2:12][CH:11]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:10]([CH2:19][N:31]2[CH2:32][CH2:33][CH:28]([CH2:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[CH2:29][CH2:30]2)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1Participants
4
Procedure
The title compound was prepared from 22 mg of 1-Benzyl-3-(SR)-formyl-4-(SR)-phenylpyrrolidine, 0.013 mL of 4-benzyl-piperidine and 24 mg of sodium triacetoxyborohydride using a procedure analogous to that described in Example 9 to provide 14 mg of the title compound. RF: 0.39 (50% EtOAc in hexanes). 1H NMR (300 MHz, CDCl3): δ1.2-1.9 (m, 8H), 2.3-3.0 (m, 11H), 3.7 (ABq, 2H), 7.1-7.4 (m, 15H). Mass Spectrum (NH3 -CI): 425.3 (M+H).
Sources & evidence
- ORD record
- ord-59eb0b2bbe0e46d4ad4b234781922f7d
- Source dataset
- uspto-grants-2000_12
- Patent number
- US06166037
Reaction notes
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